Process for the selective control of Zwitterionic amphoteric compositions

- Akzo Nobel nv

A selective process for the preparation of N-alkyl-beta aminopropionic acids (1) and N-alkyl-beta-iminodipropionic acids (II)RNHC.sub.2 H.sub.4 COOH (I)RNH(C.sub.2 H.sub.4 COOH).sub.2 (II)wherein R is a C.sub.8 to C.sub.24 hydrocarbon, said process comprising reacting an alpha, beta-unsaturated carboxylic acid in aqueous media with the corresponding primary amine of the formula R.sub.1 NH.sub.2 wherein R.sub.1 is a fatty group having 8 to 24 carbon atoms, in the presence of an organic or inorganic base having a pKb of>1<15, whereby the pH of the reaction is maintained in a range of from about 3.5 to about 5.

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Claims

1. A selective process for the preparation of N-alkyl-beta-aminopropionic acid (I)

2. The process of claim 1 wherein the pH is maintained in a range of from about 5 to about 7.

3. The process of claim 1 wherein the acid is selected from the group consisting of acrylic acid, crotonic acid, isocrotonic acid, methacrylic acid, sorbic acid, cinnamic acid, maleic acid, fumeric acid, angelic acid, itaconic acid and mixtures thereof.

4. The process of claim 1 wherein R.sub.1 is a fatty group having from 12 to 22 carbon atoms.

5. The process of claim 1 wherein the amino is selected from the group consisting of n-dodecylamine, n-hexadecylamine, n-octyldecylamine, cocoamine, tallowamine, hydrogenated tallowamine, partially hydrogenated tallowamine, oleylamine, erucylamine, behenylamine, lignocyrlamine and mixtures thereof.

6. The process of claim 1 wherein the base is selected from the group ammonia, hydroxylamine, diethylamine, methylamine, n-butylamine, glycine, aniline, alkali metal hydroxides, metal oxides and mixtures thereof.

7. The process of claim 1 wherein the reaction is conducted at a pressure of from atmospheric to about 100 psi.

8. The process of claim 6 wherein the pressure is from about atmospheric to about 50 psi.

9. The process of claim 1 wherein the acid is acrylic acid, the base is sodium hydroxide and the amine is cocoamine.

10. A composition prepared in accordance with the process of claim 1 which comprises greater than about 35 wt % N-alkyl-beta aminopropionic acid (I) based on the total dissolved solids, N-alkyl-beta iminodipropionic acids (II) and amine salt,

11. The composition of claim 10 which comprises greater than about 40 wt % of N-alkyl-beta aminopropionic acid (I) based on total solids.

12. The process of claim 1 wherein the cation of said alkali metal hydroxides is selected from the group consisting of sodium, lithium, barium, magnesium, calcium, potassium and mixtures thereof.

13. A selective process for the preparation of N-alkyl-beta iminodipropionic acid (II)

14. The process of claim 13 wherein the pH is maintained in a range of from about 4 to 5.

15. The process of claim 13 wherein the acid is selected from the group consisting of acrylic acid, crotonic acid, isocrotonic acid, methacrylic acid, sorbic acid, cinnamic acid, maleic acid, fumeric acid, angelic acid, itaconic acid and mixtures thereof.

16. The process of claim 1 wherein R.sub.1 is a fatty group having from 12 to 22 carbon atoms.

17. The process of claim 13 wherein the amine is selected from the group consisting of n-dodecylamine, n-hexadecylamine, n-octyldecylamine, cocoamine, tallowamine, hydrogenated tallowamine, partially hydrogenated tallowamine, oleylamine, erucylamine, behenylamine, lignocyrlamine and mixtures thereof.

18. The process of claim 13 wherein the base is selected from the group ammonia, hydroxylamine, diethylamine, methylamine, n-butylamine, glycine, aniline, alkali metal hydroxides, metal oxides and mixtures thereof.

Referenced Cited
U.S. Patent Documents
2195974 April 1940 Roppe et al.
2468012 April 1949 Isbell
2619467 November 1952 Isbell
2781372 February 1957 Mannheimer
2810752 October 1957 Freese
2811549 October 1957 Aelony
2816911 December 1957 Aelony
2816920 December 1957 Andersen
3133816 May 1964 Ben-Ezra
4691049 September 1, 1987 Doll et al.
5281749 January 25, 1994 Uphues et al.
5597513 January 28, 1997 Cohen
Other references
  • Chemicals Abstract, DT-2054659, dated May 10, 1972. John P. Parke, "Soaps containing nonionic cleansing agents". Unilever N.V., Germ. 1,011,555, Jul. 4, 1957. Abstract, Cohen E. US 5597513-A, date Jan. 28, 1997. Abstract, Miyoshi Yushikk, J6 1293-959-A, Dec. 24, 1986. Chem Fab Stockhausen, EP-265-818-A, dated May 4, 1988. Abstract, Tian, Zailong, "Study of N-alky beta -aminpropionate zwitterionic surfactant. Part I, Synthesis and performance test". Chinese 553243, (1991). Abstract, Hideo Marumo, Makoto Takai, Minoru Saito, Morio Ninomiya, "The preparation of metal salts of alanine, amidoamine, and diamine surface-active agents". 69(7) Kogy Kagaku Zasshi. 1306-9 (1966). Limanov, V. E., Sobol, A. F., Vornotsova, L. M., "Synthesis and antibacterial properties of ampholytic preparations based on dodecylamine", 34 Synthesis of Amino Acids, Peptides, and Proteins (1971).
Patent History
Patent number: 5922909
Type: Grant
Filed: Mar 31, 1998
Date of Patent: Jul 13, 1999
Assignee: Akzo Nobel nv (Arnhem)
Inventor: Lawrence J. Joffre (Bethel, CT)
Primary Examiner: Brian M. Burn
Assistant Examiner: Brian J. Davis
Attorney: Ralph J. Mancini
Application Number: 9/52,288
Classifications
Current U.S. Class: Nitrogen Bonded To Carbon Of Organic Radical (e.g., Amino Acids, Etc.) (562/553); Polycarboxylic (562/571)
International Classification: C07C20960; C07C22912; C07C22924;